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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSMETIN

SMILES

COc1ccc(cc1O)-c2cc(=O)c3c(cc(cc3o2)O)O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI

Molecular Formula C16H12O6
Molecular Weight 300.2635
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

Originator

Sources: DOI: 10.1002/hlca.19250080179

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Resistance of MCF-7 cells to dimethylbenz(a)anthracene-induced apoptosis is due to reduced CYP1A1 expression.
2002 Aug
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.
2002 Oct
DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells.
2003 Feb 24
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
2003 Sep 9
Antitubercular constituents of Valeriana laxiflora.
2004 Jun
Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.
2004 Nov 15
Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars.
2005 Feb
Complete assignments of NMR data of 13 hydroxymethoxyflavones.
2007 Dec
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.
2007 Feb
Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.
2008 Apr
Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.
2008 Apr 1
Effect of flavonoids on rat splenocytes, a structure-activity relationship study.
2008 Aug 15
Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.
2008 Jun
Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.
2008 Mar 15
A new ferulic acid ester and other constituents from Dracocephalum peregrinum.
2008 Oct
Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.
2009 Feb
Aurintricarboxylic acid inhibits influenza virus neuraminidase.
2009 Feb
Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.
2009 Feb 8
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.
2009 Jan 8
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.
2009 Jul
Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation.
2009 Jun
Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?
2009 Mar 16
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
2009 Mar 25
[Chemical constituents of Galium verum].
2009 Nov
[Studies on flavones from Flos Chrysanthemi Indici].
2009 Oct
Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.
2009 Sep
Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.
2010
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.
2010 Jun
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.
2015 Mar
Patents

Sample Use Guides

Mice: 50mg /kg/every other day for 6 weeks
Route of Administration: Intraperitoneal
Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:24:59 UTC 2021
Edited
by admin
on Sat Jun 26 08:24:59 UTC 2021
Record UNII
TWZ37241OT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOSMETIN
INCI   MI   WHO-DD  
INCI  
Official Name English
4'-METHYLLUTEOLIN
Common Name English
DIOSMETIN [WHO-DD]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE
Systematic Name English
DIOSMETIN [INCI]
Common Name English
DIOSMETIN [MI]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE
Systematic Name English
DIOSMETINE
Common Name English
LUTEOLIN-4'-METHYL ETHER
Common Name English
CYANIDENON-4'-METHYL ETHER 1479
Common Name English
DIOSMETOL
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-
Systematic Name English
Classification Tree Code System Code
DSLD 4156 (Number of products:7)
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
Code System Code Type Description
EVMPD
SUB35834
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
HSDB
8101
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
WIKIPEDIA
DIOSMETIN
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
EPA CompTox
520-34-3
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
PUBCHEM
5281612
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
RXCUI
1314347
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY RxNorm
CAS
520-34-3
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
FDA UNII
TWZ37241OT
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
DRUG CENTRAL
4601
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-291-8
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
MERCK INDEX
M4594
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY Merck Index
MESH
C039602
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
DRUG BANK
DB11259
Created by admin on Sat Jun 26 08:24:59 UTC 2021 , Edited by admin on Sat Jun 26 08:24:59 UTC 2021
PRIMARY
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